Sodium Acetate → 6-(2-methoxycarbonyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione

HRID 1458803Notes

Reaction equation

HRID 1458803 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[C:6](=[O:16])[NH:5]2.[CH3:17][O:18][C:19]([C:21]1(OC)[CH2:25][CH2:24][CH:23](OC)O1)=[O:20].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:17][O:18][C:19]([C:21]1[N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[C:6](=[O:16])[NH:5]3)[CH:23]=[CH:24][CH:25]=1)=[O:20]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 39809926-Amino-7-nitroquinoxaline-2,3-diolHCID 13152840Methyl 2,5-dimethoxyoxolane-2-carboxylate

Product 1

HCID 220970806-(2-methoxycarbonyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7 g (27.1 mmol) of 6-amino-7-nitro-2,3(1H,4H)-quinoxalinedione, 5.1 g (27.1 mmol) of 2-methoxycarbonyl-2,5-dimethoxytetrahydrofuran and 4.5 g (54.2 mmol) of sodium acetate in 500 ml of glacial acetic acid were refluxed for one hour. The reaction mixture was concentrated and then the crude product was purified by column chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=10/10/1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by column chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=10/10/1)

Sources & evidence

ORD record
ord-21831a645dfa41f190aaa3891d82f397
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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